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Three-component synthesis of tricyclic lactams containing the pyrrolizidin-3-one moiety

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Abstract

Tricyclic lactams containing the pyrrolizidin-3-one moiety were synthesized by the three-component reaction of aromatic aldehydes, glutamic acid (or glutamine), and N-methylmaleimide. The cascade reactions involve the stereospecific generation of azomethine ylides, the 1,3-dipolar endo- and exo-cycloaddition of a dipolarophile to the ylides, and the lactamization and afford two series of stereoisomeric pyrrolizidin-3-ones. The alkaline hydrolysis of the products of the mulitcomponent reaction gives oxopyrrolizidinedicarboxylic acid derivatives.

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Correspondence to K. V. Kudryavtsev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2318–2325, November, 2008.

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Kudryavtsev, K.V. Three-component synthesis of tricyclic lactams containing the pyrrolizidin-3-one moiety. Russ Chem Bull 57, 2364–2372 (2008). https://doi.org/10.1007/s11172-008-0337-8

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  • DOI: https://doi.org/10.1007/s11172-008-0337-8

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